The Knowledge Maturing Phase Model has been presented as a model aligning knowledge management and organizational learning. The core argument underlying the present paper is that maturing organizational know-how requires individual and collaborative reflection at work. We present an explorative interview study that analyzes reflection at the workplace in four organizations in different European countries. Our qualitative findings suggest that reflection is not equally self-evident in different settings. A deeper analysis of the findings leads to the hypothesis that different levels of maturity of processes come along with different expectations towards the workers with regard to compliance and flexibility, and to different ways of how learning at work takes place. Furthermore, reflection in situations where the processes are in early maturing phases seems to lead to consolidation of best practice, while reflection in situations where processes are highly standardized may lead to a modification of these standard processes. Therefore, in order to support the maturing of organizational know-how by providing reflection support, one should take into account the degree of standardisation of the processes in the target group.